If your Ford had a Matthew McConaughey, it would be a Lincoln


photo credit: Sotheby’s Realty

Good afternoon, sports fans. Everyone loves a good garage challenge, possibly even you. That brings us to this fine Sunday afternoon – I need an excuse to write something and hop on AutoTrader and dream a little bit, so I’ll throw down the gauntlet here. I’ll give you a back story, you tell me how you’d fill your garage. Specifics will follow below, we’ll keep to the street rules of the game:

Without further ado, let’s set the scene, shall we?

The lake air on the north side had that crisp tinge of a resilient winter despite the sun rising over the mountains early in the morning. The interior decorator stayed late last night helping to arrange the new furniture in the villa, and, after a couple glasses of wine, you decided to call it in early, exhausted from helping get the couches in the living room just right with the sculptures that were just delivered. The coffee maker took an embarrassing amount of time to figure out how to get to work, but, you have to admit, the decorator did you a solid getting the one you thought was overkill. After a delightful night’s sleep, a mug of black coffee on the new patio was the only thing that made sense in this world.

photo credit: Sotheby’s Realty

This was the first time in the last seven months that you’d had a morning free, let alone a full week wide open, at your attorney’s repeated request. The last few weeks nothing short of an assault on time itself. It was a Tuesday in September, and, after staying late at work, you noticed that the car was running a bit closer to fumes than would get you back to the grind in the morning. Rather than put it off to Wednesday morning rush hour, you stopped in, and, after overhearing your coworkers talk about the Powerball climbing north of $800 million, you were too tired to think better of it as the car filled up.

“Can’t win if you don’t play!” you remember stupidly telling the clerk that night. It was at lunch the next day when you pulled out your debit card to pay the clerk that you saw your ticket peeking out, feeling a bit sheepish for not going in with your coworkers’ pool. The next couple of hours are lost to your memory, but you remember spending an inordinate amount of time at the booth at the sub shop staring from your phone back to the ticket and back to your phone again. Your coworkers later figured out what happened when you went home sick and phoned in your two weeks’ notice on Thursday morning. Everything only sped up from there.

Google was your best friend that night. First thing in the morning, the phone calls started. Then the meetings. The first was to an attorney buddy of a buddy, who gave you explicit instructions on a two-hour call to follow over the next couple of weeks. A financial planner and estate lawyers meant fancy lunches where nobody drank except for you. You gave your early 60-day notice to the apartment complex and went month-to-month, grabbing a hotel room under a name your attorney had set up downtown. A new phone showed up within a week, registered to your new LLC, after the newspaper interview broke and you started to hear from family members that you don’t remember talking to since Y2K.


Brokerage accounts sprung to life and legally binding agreements were filed to set up a new trust with some nondescript acronym in the Cayman Islands. Days spent learning legalese melted into nights studying the financial acronyms you were expected to know the next morning.

The New Year snuck up on you, and, one Friday night in early January after a whirlwind week, your attorney took you aside after she saw you day dreaming while on a conference call discussing the future foundation you were setting up to get your tax situation right. “You need a drink, and then vacation, in that order. Let’s talk.”


At the bar, she told you that her best advice she had for newly minted multimillionaires was to begin their real estate portfolio – out of the country where your cellphone plan didn’t work and nobody knew your face. You woke up the next morning to an email from her with a link to the Sotheby’s website. Some absurd properties you wouldn’t even comprehend, but with a net worth suddenly deep into nine figures, it was time to make that first stupid purchase.

After a weekend staying in at the house picking out something that wasn’t too ostentatious but certainly wasn’t subtle, you sent a link to your attorney and inside of a month and no less than two hundred signatures of your own damn name, the deed for the perfect 6,458 square foot villa on the north side of Lake Como was in your attorney’s safe at her office.


The contractors and interior designers and art curators were a beating, but a welcome change of gear from the financial dorks and law nerds you spend time with all winter. It was only last week that you got the keys from a very excitable Italian real estate agent to survey your new summer getaway.

photo credit: Sotheby’s Realty

The kitchen still smelled like some new construction they’d done to bring the villa into this century, but out here on the patio the only thing you could hear was the wind lapping at the infinity pool below and the occasional speedboat going for a morning run out of the marina. Seeing the keys on the table to your rented Fiat, you were reminded that you only had three weeks left before you had to return the car to the company.


Opening your laptop and checking your calendar to see nothing for the next week, it was time to finally get to the business of making some obnoxious rich person decisions. The contractors had put a lift in the three-car garage, giving you room for 4 cars inside, and you had a single spot on the street for one car parked outside. While the former owner hadn’t used the boat launch at the edge of the lake, having a whole spring of nothing to do but learn Italian and get your bearings while your foundation got off the ground meant it was time to learn how to be one of those nautical people – this was Lake Como after all.

Taking a sip of coffee, you crack your knuckles and fire up the eBay to make some bad decisions.



  • Five vehicles in total, with no upper price limit: Four cars/trucks/SUVs/El Caminos to park indoors, one outside on the street. Custom builds are welcomed, but require specifics – if you’ve retained Jonathan Ward at Icon Customs to build you a Derelict, we will need some details on the commission
  • One must, as you wrestle with your new sense of wealth, be valued at more than $1,000,000 United States dollars
  • Bonus round: one boat suitable for use on Lake Como. The build date on your yacht at Blohm+Voss is not until the fall, although you have a meeting with them at their headquarters in Hamburg in May. You’ll need something adequate for summer use.
  • Any source of sale is acceptable: Craigslist, eBay, AutoTrader, Cars.com, whatever works for you works for me
  • Currently available for sale or prices within last three years are acceptable to stick within price limits
  • Post links or pictures or both, but let’s cite some sources here, folks
  • Submissions will be graded on creativity through the week

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